Extreme Mature Tranny Prostitute Story free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
"Hi honey, are we all set?"
"Yes babe, I'll be round in about half an hour"
"Is it as we planned?"
"Pretty much, yes. Are you dressed as I said?"
"To the letter, hon"
"Good. I'll see you in about 30 minutes. Thanks for this."
"No : thank you".
Dave was such a good, regular client. He always phoned when he said he was going to phone and never let me down for a meet when he had booked. Once he had booked an hour of my time but had hAd his shifts changed at work, and he had worked nights the night before. He still turned up for his meeting, and we just sat drinking coffee and chatting. I just gave him a courtesy blow job before he left as I had to at least empty him of his seed no natter how tired he was!
Tonight was no exception: he had phoned exactly on time. Now it was for me to fulfill my side of the deal and dress to please him. For this meeting he had requested a very precise outfit, with exacting details.
Dave hung up the phone, a dry cold smile adorned his hard, rugged face.
He has been seeing Tina regularly for about 5 years. She was everything he needed in an escort, and sometimes a lot more! In his mid fifties, and divorced from his ex wife for many years he longed for a physical relationship and sought his fun in the form of prostitutes. Like so many others, once he reached around 40 he had admitted he was actually bi sexual and had interactions with many cross dressers at various dogging locations and public toilets, before he actively searched for a 'real' transvestite escort on the internet.
After trying a few out, he found Tina and had never been with any other since, as she met his very exacting and often changing demands with so much enthusiasm, he didn't need to get his kicks from anywhere else.
He had been sat in the car park for some. 20 minutes or so, and had seen a steady stream of guys of varying ages sizes and statures, enter the cottage one by one. A few had left but he estimated that there must be at least five in there.
Crossing my legs to zip up my black PVC knee high boots, I held the cigarette in my lips whilst I struggled with the awkward zips. Finally achieving my aim, I pulled the boots up to their full extent and stood in front of the mirror and admired the view.
I felt at ease dressed like this. I loved dressing to order.
My seamed black stockings were positioned perfectly: the seams running down the centre of both legs, dissapearing into the sexy black boots.
The clips on my burlesque cup less basque were metal, like in the 70s. Very sexy. My boobs were pushed up and together. This basque made them look absolutely fantastic, Dave was going to be impressed. My thick pearl necklace and dangly pearl earrings also enhanced my appearance - but what completely rounded off my look was my make up. Just as he had asked I had my make up 'heavy'. Lots of foundation followed by masses of face powder. My blusher was dark brown, sweeping up over my cheek bones. My eyes were coated in bright blue eye shadow and I wore thick black eye liner. Finally, my lips were over painted in bright red sticky glossy lipstick, and were lined with a dark red lip lining pencil. Yes! I had certainly achieved the. 70s porn star look that he had requested in his telephone booking some three days before.
Dave picked up the portfolio folder off the passenger seat of his car and opened his door to make the short walk to the cottage.
As he did this the interior light of his car came on, and he quickly rolled up the folder before closing the door on his exit.
As he got into the cottage it was a normal scene from a sex cottage. Lots of dark dimly lit figures milling about whilst two men were stood side by side at the 'troughs' obviously playing with each other's cocks.
Dave was an expert at this. So confident and assured.
"Anybody like trannies?" He asked loudly. All movement stopped in the place and although he didn't get any verbal answers he had their attention.
"I'm talking about a good tranny. She looks like a whore... Here's her pictures." He passed the folder to the nearest guy.
"She lives about three minutes drive away and is ready for anyone right now.
"Fucking hell!" Said the guy flicking through the pages of the folder.
"Is this for real?"

Same as Extreme Mature Tranny Prostitute Story Videos

2 years ago
  • 0
  • 9
  • 0

Mature Extreme Tranny Prostitute Part 2

‘Yes, but I’m not messing about. If you would like to come then follow me now. I will explain what will happen when we get outside. ‘ The folder was quickly passed around the five of them, each of them looking at each other- silently asking – should we or shouldn’t we? Dave stood by his car knowing that at least some of them would come. Eventually, one by one they emerged and started to walk over to Daves car. I moved the sofa into the centre of the room. It was now facing directly away...

1 year ago
  • 0
  • 9
  • 0

Mature Extreme Tranny Prostitute Part 3

I heard someone unbuckling his belt and shuffling behind me. He was obviously getting into position. I felt a strong pair of hands on my buttocks opening me up before I felt a hardness inside me. His cock was quite thick and extremely hard although it wasn't very long. He held my hips as he pumped into me. My eyes were closed tight as he pushed himself into me. He was gasping and groaning as he pumped me full of his meat. He only fucked me for a minute or so when I felt him withdraw. "Go on...

2 years ago
  • 0
  • 5
  • 0

Mature Extreme Tranny Prostitute Part 2

"Yes, but I'm not messing about. If you would like to come then follow me now. I will explain what will happen when we get outside. " The folder was quickly passed around the five of them, each of them looking at each other- silently asking - should we or shouldn't we? Dave stood by his car knowing that at least some of them would come. Eventually, one by one they emerged and started to walk over to Daves car. I moved the sofa into the centre of the room. It was now facing directly away from...

1 year ago
  • 0
  • 9
  • 0

Tranny

What do you think “Sluts with Nuts 4,” “One Hung Bitch,” and “My Girlfriend is my Boyfriend” all have in common? If you guessed they all had tranny babes doing kinky shit, then you were right. All of those titles are from DVDs that you can view for absolutely free on the site I have for you this time around. What’s not to love about watching some thick dicked chick fuck some hot bitch in the ass? I get that it’s not everyone’s cup of tea, but damn you’re missing out on some good shit if you...

Premium Shemale Porn Sites
3 years ago
  • 0
  • 9
  • 0

The Cabbie and The Tranny

The Cabbie and The Tranny By Michele Nylons Twas the middle of Manchester one winter night; and the only cab on the rank, The driver was reading a 'Score' magazine; whilst quietly enjoying a wank. He was dreaming that Venus was kissing his penis; and the shaking was making him tired, When a tranny called Lena, with false tits like Sabrina; came over and gently enquired. "How much to Oldham" she said; well the cab driver nearly dropped dead! He got such a shock he let go of his cock;...

2 years ago
  • 0
  • 19
  • 0

Tranny Boy Posse Tales of the Evil FagHag

This is just a story, okay? I don't advocate having sex with underage people and I realize that probably most cross-dressers aren't gay. Yeah, and most females who choose to hang around gay dudes aren't evil either. Most 'fag-hags' seem to be nice people and some may even resent that term of endearment. And it's never been my intention of slandering the Vegan lifestyle, Wicca, Druids, the rest of the occult and all the other great religions of the world. This is just a story, okay? It...

2 years ago
  • 0
  • 16
  • 0

Tranny Motel

Tyrone and Kimberly Woods kissed as all of the guests at their house party cheered them on. It was their first anniversary and they were celebrating this night with family and friends. There were close to forty people in attendance – most of whom had brought some form of alcohol and all of whom had brought a gift. There was great music and excellent barbecue as Kimberly’s dad and Tyrone’s uncle manned the grill. Folks were laughing, dancing, and having a great time. In one corner of the yard,...

4 years ago
  • 0
  • 17
  • 0

SARAHS NINE INCH TRANNY

For the last week my man has been tempting me with images of hung trannys. They have an added dimension when it comes to sex - tits and a cock, preferably both in generous doses. By the end of the week I am hanging out to experience a new one. One of the images he showed me was a side on shot of a tranny in panty hose with her back to the wall flaunting a huge erection thrusting out of her panty hose that really piqued my already strong libido. Another was a pic of tall slim tranny sitting...

3 years ago
  • 0
  • 16
  • 0

SARAHS NINE INCH TRANNY

For the last week my man has been tempting me with images of hung trannys. They have an added dimension when it comes to sex - tits and a cock, preferably both in generous doses. By the end of the week I am hanging out to experience a new one. One of the images he showed me was a side on shot of a tranny in panty hose with her back to the wall flaunting a huge erection thrusting out of her panty hose that really piqued my already strong libido. Another was a pic of tall, slim tranny sitting...

2 years ago
  • 0
  • 12
  • 0

TRANNY THREESOME

“Ask me again baby,” he groans as he supports himself above me on his hands and toes and frantically slides his full eight-inches into me. “Would you like to blow a tranny while I watch?” “Yes, baby yes, so fucking good, yes,” he moans as we orgasm together. I had just the tranny, Rosie, in mind, I hadn’t told Roger but she propositioned me recently and hinted that she would enjoy me and Roger at the same time. We always go to some trouble to dress or undress to turn on our guest when they...

1 year ago
  • 0
  • 10
  • 0

Slovene Tranny and Her American Men

Milena Dorin awakened from her slumber. She grabbed her iPhone and pressed the button to see the time. It was 6:14 a.m. She decided to get up and bathe. She walked into the master bathroom of her palatial two-bedroom, two-bath downtown condo. She pulled her douching apparatus from beneath the sink. She cleaned out her 40-inch ass. After completing that task, she hopped in the shower. The steamy, hot water felt good against her milky-white skin. She scrubbed her curvaceous figure with a purple...

3 years ago
  • 0
  • 10
  • 0

TRANNY THREESOME

“Ask me again baby,” he groans as he supports himself above me on his hands and toes and frantically slides his full eight-inches into me. “Would you like to blow a tranny while I watch?” “Yes, baby yes, so fucking good, yes,” he moans as we orgasm together. I had just the tranny, Rosie, in mind, I hadn’t told Roger but she propositioned me recently and hinted that she would enjoy me and Roger at the same time. We always go to some trouble to dress or undress to turn on our guest when they...

3 years ago
  • 0
  • 106
  • 0

My 31st prostitutemdashtall and mature

The 31st prostitute I saw was a very, very tall woman standing at about 6’ 2. Physically similar to Geena Davis or Kristen Johnston, but with a slightly bigger bust, a mature woman in her 40’s. Taller than me, and younger than me, her prices were a bit out of my league. I don’t usually see escorts that expensive, but the curiosity got the best of me. I set up an appointment with her for the following day. She was staying at one of the more upscale hotels in town. I parked and took the elevator...

3 years ago
  • 0
  • 17
  • 0

Tranny in Croatia

I started crossdressing as a teenager. I had a young mom, who always had some interesting and sexy clothes. I was 13 the first time I took her clothes (she was 31 at the time). I took a metallic silver jacket and some lacy thongs, and I put on her pink lipstick. I took a couple of photos, but they all came out blurry. But I liked how it felt, the only trouble was I did not know what to do... it felt wrong enough to hide it but right enough to get me interested. I dressed up quite often, but not...

4 years ago
  • 0
  • 15
  • 0

Riverbank Tranny Fucktoy

Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river. It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site. I had been chatting to Fillipe for a couple of hours, and we were both getting hornier and hornier with each new message that we sent. It was me that asked if he would like to meet that night, and he of course said yes....

1 year ago
  • 0
  • 8
  • 0

Sissy Tranny Annie Slutty Fantasy

I have been dressing since an early age, dressing in my mothers stockings, suspender belt, bra, panties and heels. I used to feel my smooth legs and my cock would get hard straight away. I love how my cock looks when im dressed as a sissy slut and from that early age all ive ever wanted is to have a horny guy in front of me, with his cock hard knowing that he wants to fuck me. My fantasy and dressing got a lot more sluttier when I first in with my first love. Her name was Claire and she loved...

1 year ago
  • 0
  • 12
  • 0

My black tranny wife part 3 final

Heather's dress or lack of was amazing. It was white and floor length in the back. It was open down far enough exposing half of her tight ass. The front was cut open down to her naval it was covered in very sheer lace, so the inside of her tits and her cleavage were easy to see. From her waist down, it was also open. She was wearing a sheer G-string. She must have been excited because you dick was semi hard and it really filled out her panties. If you looked close enough you could see her dick...

3 years ago
  • 0
  • 27
  • 0

First time with a Tranny

Stevie had always found it relatively easy to get girl friends. Not all had been good experiences. He always felt that after sex he just wasn’t satisfied. Maybe he wanted something different. Some people are perfectly fine about being gay or bisexual, but for others, it is a scary mine field. Stevie was one of those people. People had commented on him being gay for years and he always felt ashamed. He denied it, of course, but as time went by the thoughts about the whole subject haunted him. He...

Gay Male
1 year ago
  • 0
  • 20
  • 0

Young Tranny at Great Grandmas Funeral

“What’s going on,” inquired the 34 year-old construction and building inspector.“Nothing,” smiled the high school senior with the 22-inch dark brown wavy hair extensions and gray contacts. “What’s up with you.”“I want summa that.” he leaned forward trapping her between his heaving chest and the counter.“What?”“That sweet potato pie over there,” he winked.“Oh, okay! I’ll cut you a piece.”“You do that,” he said not moving an inch and running a forefinger down her weave.She darted her eyes away,...

3 years ago
  • 0
  • 8
  • 0

Threesome with a tranny and a woman

I have a friend with benefits that I have been with for a few months. Her name is Bree and she is a tranny. I figured out I was Bi a few years ago so I started looking around for guy's to have sex with. Like others, I found guys who seemed to want to get together but would not pan out for some reason or another. That's when I discovered tranny's and new I wanted to be with one. So I started to look around for one and that's when I met Bree. She was beautiful 5'3" tall, dark hair and a tight...

1 year ago
  • 0
  • 9
  • 0

Nate and his tranny neighbour

My first ever story. Depicting sex between a man and a transsexual.It is lengthy but personally I enjoy these best. Constructive feedback is greatly appreciated, so feel free to write to me. Enjoy ; )Nathan (Nate for short) was an average eighteen year old boy; liked girls, sports, partying, and being on his summer holidays he enjoyed the time off school. With some exceptions to the average rule, he loved his kinky dirty thoughts and porn. Frequently watching shemale porn, gorgeous busty women...

1 year ago
  • 0
  • 6
  • 0

My first but not last encounter with a tranny

My Wife and I have been married for about 3 years now and have since recently, been looking to have our first experience with a she male. I met a girl online name Judy and after chatting for a while and exchanging pictures we agreed to a meet and greet. Judy proved to be a very sexy transgender with feminine features. Her highlighted hair was long and she had size B cup breast with a thick firm ass and long pretty legs. She was very beautiful and had an awesome personality. We sat down and...

She Males
3 years ago
  • 0
  • 13
  • 0

Tranny Wife Me

I have always loved sex with trannies, even more than sex. Friendship and closeness that I would struggle to fin in a guy. My wife had no huge preference for Tgirls but she did have a ravenous appetite for sex and was curious enough to try everything. We decided to go to Manchester and their regular Saturday night Tranny evenings and from previous visits, we had a few drinks in Napoleon's Lounge. It was a popular meeting place for "girls." Trannies who liked other girls, trannies who preferred...

2 years ago
  • 0
  • 11
  • 0

My first tranny

I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the...

3 years ago
  • 0
  • 7
  • 0

My first time with a tranny

I always had a strong sex drive, and since I had been around 16 I had been turned on by gay porn. I must say that I am straight, well on second thought, better say that I am bisexual. And I always have and will like girls. But there is something about a cock that turns me on and I then discovered shemale porn. I think that a hot sexy shemale and a cock is the best combination there could be. I have a strange fascination with cocks and a hot sexy girly body tops it off.In August 2007 I was 24...

1 year ago
  • 0
  • 12
  • 0

Dream Tranny

Dreams can be strange, sexy things. Your wife may be a stunning knock-out, way the fuck out of your league, but I bet she ain’t your dream girl. No, your perfect fantasy angel has the big tits and pretty face you love so much, but she’s also got something extra: a big ol’ dick between her legs. Sorry, wifey, but tonight may be a good evening to spend with DreamTranny.DreamTranny.com is a site with history. They’ve been around since 2000, making them one of the older shemale porn operations on...

Premium Shemale Porn Sites
2 years ago
  • 0
  • 9
  • 0

Stag Night Tranny Gang Bang

I really still don’t know why, to this day, i said i would go with Ross to the Stag night. It was probably one of my more stupid decisions in life!! I’d met Ross a couple of times before, mostly at the S Club in Merton. Ross was about twenty three, really good looking, and loved the whole cross dressing scene but didn’t dress himself and described himself as an ardent ‘admirer’. He’d approached me at the bar one night and we’d got talking. Although I was much much older than him it only seemed...

2 years ago
  • 0
  • 6
  • 0

Stag Night Tranny Gang Bang

I really still don't know why, to this day, i said i would go with Ross to the Stag night. It was probably one of my more stupid decisions in life!!I'd met Ross a couple of times before, mostly at the S Club in Merton. Ross was about twenty three, really good looking, and loved the whole cross dressing scene but didn't dress himself and described himself as an ardent 'admirer'. He'd approached me at the bar one night and we'd got talking. Although I was much much older than him it only seemed...

3 years ago
  • 0
  • 11
  • 0

Couple Finds Another Plus Tranny

While I was in the military, there were many opportunities to see some of the wild and crazy sites and people of the world. One time in Japan a bunch of us in a mixed group (men and women) went to a show that featured transsexuals. These were men who now dressed and acted like women. All of the men/women featured had breast implants to additionally make you believe they were real. The show was very exciting with each of the trannies on stage showing us they were as good looking without their...

1 year ago
  • 0
  • 16
  • 0

First Time with Tranny

So this is the story about how I got my first experience being a bottom, and why it was with a tranny.I was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the...

4 years ago
  • 0
  • 28
  • 0

Im a Meat Packing Girl Tranny

I didn't go looking for a tranny, shemale, dickgirl, or whatever derogatory term a homophobic world has labeled women that happen to be packing a penis. In fact, while I had messed around a little with the man worm, back in college and with a drunken buddy a few times, I considered myself 100% a hetero male, in love with the female form and a total horn dog for a beautiful woman. I must admit, I've jerked off more than a few times to shemale porn on my computer at home, wondering what it would...

1 year ago
  • 0
  • 29
  • 0

My Tranny Schoolgirl Fantasy

As I sat on my couch, i was thinking, "Being alone doesn't have good perks. Maybe if I wanted to dream something naughty, it might be cool." So, I closed my eyes, and I dreamed of a very naughty tranny schoolgirl who would do what i like. All of a sudden, I heard a sexy female voice say to me, "Hey Brian, you bad boy, you big stud." I woke up, and there was this hot tranny girl who was dressed as a naughty tranny schoolgirl. She had nice lovely pigtails, a very sexy tied tight white top, in...

3 years ago
  • 0
  • 6
  • 0

My first time as a bottom and with a tranny

So this is the story about how i got my first experience being a bottom, and why it was with a trannyI was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the...

3 years ago
  • 0
  • 7
  • 0

Nate and his tranny neighbour Part 3

Nate and his transsexual neighbour part three, as always hope you freaks enjoy and let me know what you think ; ) Nate woke up thinking about his last two encounters with his hot big-dicked neighbour. Having never had much experience with woman to having the hottest sex he could hope for was a dream come true. However as he slowly stroked his hard morning wood he realised he had yet to fuck Jez, her gorgeous tight ass in lycra was a vision to behold. Wanting nothing more to feel her pretty...

1 year ago
  • 0
  • 10
  • 0

Fun with a latina tranny

So I'm a big fan of a big tranny cock in my ass. Just throwing that out there early on here.So this past summer I decided that with my school being off I should get some tranny cock as fast as I could. I went on a site and set up a new account, hoping for the same luck I had a few months ago with a hot black tranny named Jade and her friend. I quickly found a very nice 20 something tranny names Maria who said I would do. We went through a few chat sessions, with our cams on and I convinced...

3 years ago
  • 0
  • 12
  • 0

Amy The Tranny Chapter 1

I met Amy at an adult theatre in town.She was dressed to nines in a mini skirt, tight halter top, and pumps leading up a pair of fishnet clad legs. I invited her into a private boothand once inside, went over her price for someadult fun. She told me I couldn't fuck her as shewas on her period but I knew something was up and asked her flat out if she was a tranny. She looked at me wearily and slowly nodded her head. I assured her I was into tranny sex and she relaxed and asked if I was into just...

4 years ago
  • 0
  • 9
  • 0

Tranny Delight

I had been feeling particularly horny one day and waiting for Joe to come home I got to thinking about having sex with a black woman and then watching as Joe took her and then thought even more that perhaps a black tranny might be a bit more fun. So when Joe came home I easily talked him into going down to the alternative nightclub we had visited once before and off we went. Upon entering the club I saw that it was as crowded as usual and Joe and I took up a small table and settled with our...

3 years ago
  • 0
  • 11
  • 0

The Perils of Pauline Tranny at the Truck Stop

Paul sat behind the wheel of his Mustang, the windscreen opaque with heavy rain. It had been raining hard for the last hour and he was hoping it would have stopped before he reached the truck stop. He looked through the windshield as the wipers lazily swept back and forth across the glass. The sodium vapour lamps bathed the parking lot in an orange hue. The blacktop was slick with rain and puddles had formed in the numerous potholes. The lot was quiet; as it usually was at 8:30pm on a Tuesday...

1 year ago
  • 0
  • 11
  • 0

Revenge on a Tranny

Revenge on a Tranny My relationship with my partner Julie had been strained over the last twoof our ten years together. For a period of six months we?d stopped having sex.I thought she might leave me but I figured that if she was going to find anotherwoman then there was nothing I could do about it and besides, I had a womanor two I knew I could fall back on for affection if I ever found the need.I was a good lover, but there seemed to be something that Julie needed sexuallythat I couldn?t...

2 years ago
  • 0
  • 10
  • 0

Mary the PROSTITUTE WHORE her side of the story

     This is iIn response to my story named    How I got my wife to become a PROSTITUTE & A WHORE                           Today I received a nice note from   a friend.   Here is a copy of it. fantastic story you wrote, plaese give regards to mary, I hope one day she will tell her side off the story.       Well I thought that was a great idea so I asked Mary herself to let you know what she thought.       First of all before Mary gives you her side of the story I want to make a few...

1 year ago
  • 0
  • 7
  • 0

Mary the PROSTITUTE WHORE her side of the story

     This is iIn response to my story named    How I got my wife to become a PROSTITUTE & A WHORE                           Today I received a nice note from   a friend.   Here is a copy of it. fantastic story you wrote, plaese give regards to mary, I hope one day she will tell her side off the story.       Well I thought that was a great idea so I asked Mary herself to let you know what she thought.       First of all before Mary gives you her...

Voyeur
2 years ago
  • 0
  • 9
  • 0

Flat Mates Chapter 2 My first visit to a Tranny Club

FLAT MATES Chapter 2: My first visit to a Tranny Club Having told Gloria that everything was "cool" between us, she then proceeded to shock me with her next statement. "If you wouldn't be embarrassed to be seen out in public with me," Gloria continued, "why don't you come with me to the club tonight? The band you say you like so much are playing again and I am sure you would enjoy yourself." "I'm not sure," I answered. "I would really like to hear the band but I'm not confident...

1 year ago
  • 0
  • 9
  • 0

Truck Stop Tranny Sluts

My girlfriend and lover Candi and I were driving back to her place for some steamy tranny sex after a night of partying at a tranny/gay bar in town when we passed a truck stop on the highway. Buzzed and horny as we were, we laughed about stopping in the lot and doing so hookin’ as a means to get us some trucker cock. After a minute or two of silence, Candi said lets do it and before I could answer she was turning back for the truck stop! Candi and I are both bisexual crossdressers and we pass...

Crossdressing
1 year ago
  • 0
  • 91
  • 0

Mom Is A Prostitute ndash Part I

writing this story about my hot mom BHANUMATHI, usually called BHANU. In this story I tell you how she became a prostitute. BHANU mom has a fair complexion, her vital stats are 38-30-40. She is now 39 years old. She was the marketing manager in a MNC firm before she became a prostitute. She has taught me sex at a very young age of 8 and how I came through her pussy to this world.After finishing dinner at the restaurant at night 10 O’clock, mom and I were walking towards home. Mom looked very...

3 years ago
  • 0
  • 12
  • 0

Tranny in Toronto Chapter 2

Introduction: Read first two stories on my profile. I cant seem to find the conversation we had by e-mail. ~~~ Since I lost my virginity to a couple I met on Craigslist (read my past story) and I not only had a wonderful time, but got paid as well, I decided to post my own ad on Craigslist. It was a simple ad, a tranny in Toronto looking for fun time. He saw my ad on Craigslist and decided to message me to see whether or not we could get together or not. His name was Marc, a young black boy...

1 year ago
  • 0
  • 12
  • 0

My first time with a tranny

It happened on a Monday morning. After waking up with a throbbing hard-on. I called up my regular booty call. But she couldn't make it. Because her husband stayed home from work that day. So I decided to browse Craigslist, looking for someone local. After posting my ad, looking for NSA sex. I sat back and waited. Within minutes, I received over a dozen new messages. But none of them really appealed to me. Then after a few hours of receiving numerous messages, from both women and...

2 years ago
  • 0
  • 10
  • 0

Tranny in Toronto Chapter 2

~~~ Since I lost my virginity to a couple I met on Craigslist (read my past story) and I not only had a wonderful time, but got paid as well, I decided to post my own ad on Craigslist. It was a simple ad, a tranny in Toronto looking for fun time. He saw my ad on Craigslist and decided to message me to see whether or not we could get together or not. His name was Marc, a young black boy who lived in Scarborough. He said he was a shy guy, a virgin, and he watched a lot of tranny videos...

2 years ago
  • 0
  • 8
  • 0

Alan Gets A Tranny

-------------------------------------------------------------------------- I went to Alan's house after work one day to talk to him. His mom was single and she need a male figure to discuss masturbation since she had caught him doing it. I rang the bell. I heard footsteps on the stairs and then the door opened. "Hi Alan." "Oh, hi Mr. Jones." “Can i come in?” “Sure,” he said holding the door open. “Alan I have to be home soon, so let me just say this quickly: I know your mom caught...

2 years ago
  • 0
  • 6
  • 0

First Time With Tranny

I had fantasized for quite a while about hooking up with a hot chick with a nice cock. I gravitated towards shemale porn and couldn’t get enough of it. On this particular day I was having a few drinks and browsing the web for my favorite shemale movies. I discovered the gay.com chat forum. Soon I was chatting with this hot asian crossdresser. She was about my age (21 or so at the time) and lived just a few towns over from me. We shared some fantasies and seemed to have a good connection. She...

3 years ago
  • 0
  • 17
  • 0

My Tranny Teacher 4

This is a fantasy story. Every day left me feeling more horny and excited for our next tutoring session with Ms. Bennett (Becca). I was hard about 90% of the time just going thru all of my special clothing and deciding what I could get away with wearing to school that would light up my teacher and make her clitty into a full stiff dick that I could put to use. After looking at everything I decided that black lace top stockings would be exciting and could not be noticed under my school clothes....

3 years ago
  • 0
  • 11
  • 0

Threesome with a tranny and a woman part 2

I had just finished fucking and sucking with Bree ( the tranny) and Tammy ( the woman) and we all wanted more. If you did not read the first story please do that so you know what's going on. We were laying there getting our breath back and I looked at Tammy. Now that I knew she was a woman I really looked her over. She was about 5'3" with a fantastic body and shoulder length blonde hair. She had big tits with extra large nipples that looked like pencil erasers only longer. She had a little...

1 year ago
  • 0
  • 19
  • 0

Tranny Arschfick in der Jugendherberge

Fabianes ersten ErfahrungenFabiane, die ursprünglich einmal Fabian hieß, war eine Tranny und hatte gerade ihren 20. Geburtstag gefeiert. Sie war Berufsschülerin. Als solche übernachtete sie regelmäßig die Woche über in dem Hotel, in dem ich an der Rezeption arbeitete. Dieses Hotel war zwar an sich eine Jugendherberge, aber ganz im Stiele eines Hotels. Somit hatte ich mit vielen jungen, coolen Menschen zu tun. Mit einigen entwickelten sich manchmal Freundschaften, so auch mit Fabiane. Sie kannte...

3 years ago
  • 0
  • 20
  • 0

Trucker the Tranny

Jermaine Simpson drove his white 2010 Peterbilt raised-roof big rig into the truck stop just outside of the city. He called his friend, Mariah.“Hey, baby,” the dark-skinned transsexual answered.“What’s up boo? I’m at the truck stop,” Jermaine shared.“Okay, oool! I’m on my way.”“Awesome! Can I get a shower at your house?”“Of course!”“See you in a few.”“Bet!”Jermaine’s nine-and-a-half-incher was already hard. He loved fucking her whenever he was down this way. Once he had taken her on a six-day...

4 years ago
  • 0
  • 13
  • 0

BuildaTranny

Garvey Williams kissed the pretty, effeminate, white boy he had had been secretly fucking since they were high school sophomores. Back then, Garvey was a standout wide receiver with high prospects of moving on to Division One. He had progressed as everyone thought and Jamie Collier, the femboi, followed him to the large state university. Garvey and the Mustangs earned a national championship his junior year. The football prodigy decided that he should enter the NFL draft immediately following...

4 years ago
  • 0
  • 5
  • 0

My first tranny girl experience got me hooked

I have always wanted to have sex with a tranny. I find these women sexy. In my daily life I dont know any, so I look online find a tranny to fuck. As I look online I find a sexy Cuban t-girl advertising sex. I instantly give her a call and arrange a time to go meet. One thing that turned me on is that she just moved from Cuba and had an spanish accent that turned my dick rock hard. Once I get to her home she leads me to the bedroom. She is 5'5 about 125 pounds. My girlfriend is 5'9 160. So my...

1 year ago
  • 0
  • 11
  • 0

Fun Time With A Top Tranny

So since I got a good rating for my first sex story, I shall write another one about my first time with a tranny. This happened last year. She was 25, and I was 21. So I am Ash, I am 22, I pretty good and masculine looking. I am mostly a bottom though. I have always been a huge fan of shemales and ladyboys. Respect them and also lust for them :p anyway, so I was in dubai last year and I thought that there might be much more shemales and easier to meet since the place was quite forward with a...

Gay Male
3 years ago
  • 0
  • 9
  • 0

Tranny Night

Tranny Night: My name is Andrew and I had known Jane since we were very young. She was a precocious child and could play piano and read music from a very early age as well as reading complex novels when most children our age were struggling with reading Enid Blyton novels. I was the brightest boy in our class and would have liked to pretend I was the brightest pupil in the class but Jane's results were always better than mine, although I would not admit it as she was a girl. As...

3 years ago
  • 0
  • 8
  • 0

First Time With Tranny

I had fantasized for quite a while about hooking up with a hot chick with a nice cock. I gravitated towards shemale porn and couldn't get enough of it. On this particular day I was having a few drinks and browsing the web for my favorite shemale movies. I discovered the gay.com chat forum. Soon I was chatting with this hot asian crossdresser. She was about my age (21 or so at the time) and lived just a few towns over from me. We shared some fantasies and seemed to have a good connection. She...

Porn Trends